Water → HCID 178441395, compound

HRID 1493671Notes

Reaction equation

HRID 1493671 reaction equation
[C:1]([OH:18])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O.[CH3:20][CH2:21][CH2:22][CH2:23][CH:24]1[C:59](=[O:60])[O:58][CH:57]([CH:61]([CH:63]([OH:71])[CH2:64][CH2:65][CH2:66][NH:67][C:68]([NH2:70])=[NH:69])[CH3:62])[CH:56]([CH3:72])[CH:55]=[C:54]([CH3:73])[CH2:53][CH2:52][CH2:51][CH2:50][CH:49]([OH:74])[CH2:48][CH:47]([OH:75])[CH2:46][CH:45]([OH:76])[CH2:44][CH:43]([OH:77])[CH2:42][CH:41]([OH:78])[CH:40]([O:79][C@H:80]2[O:84][C@H:83]([CH2:85][OH:86])[C@@H:82]([OH:87])[C@@H:81]2[OH:88])[CH:39]=[C:38]([CH3:89])[CH:37]([OH:90])[CH2:36][CH2:35][CH2:34][CH:33]([OH:91])[CH2:32][CH2:31][CH2:30][CH:29]([OH:92])[CH2:28][CH2:27][CH:26]([CH3:93])[CH:25]1[OH:94].S([O-])([O-])(=O)=O.C([O-])(=O)CCCCCCCCCCCCCCC.[Ba+2].C([O-])(=O)CCCCCCCCCCCCCCC>CO>[CH3:20][CH2:21][CH2:22][CH2:23][CH:24]1[C:59](=[O:60])[O:58][CH:57]([CH:61]([CH:63]([OH:71])[CH2:64][CH2:65][CH2:66][NH:67][C:68]([NH2:70])=[NH:69])[CH3:62])[CH:56]([CH3:72])[CH:55]=[C:54]([CH3:73])[CH2:53][CH2:52][CH2:51][CH2:50][CH:49]([OH:74])[CH2:48][CH:47]([OH:75])[CH2:46][CH:45]([OH:76])[CH2:44][CH:43]([OH:77])[CH2:42][CH:41]([OH:78])[CH:40]([O:79][C@H:80]2[O:84][C@H:83]([CH2:85][OH:86])[C@@H:82]([OH:87])[C@@H:81]2[OH:88])[CH:39]=[C:38]([CH3:89])[CH:37]([OH:90])[CH2:36][CH2:35][CH2:34][CH:33]([OH:91])[CH2:32][CH2:31][CH2:30][CH:29]([OH:92])[CH2:28][CH2:27][CH:26]([CH3:93])[CH:25]1[OH:94].[C:1]([O-:18])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 985Palmitic Acid2×HCID 161420Barium palmitateHCID 178441404HCID 178441404, compound

Product 1

HCID 178441395HCID 178441395, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.22 g (0.887 millimoles) of palmitic acid are dissolved in 15 ml of methanol and so much water is added dropwise to the solution that the palmitic acid should not precipitate. To the solution thus obtained 2.51 ml of a saturated barium hydroxide solution are added. The precipitated barium salt is filtered and added to a suspension of of 1.0 g (0.887 millimoles) of primycin sulfate and 120 ml of methanol. The reaction mixture is heated to boiling for an hour whereby the barium palmitate is dissolved and the insoluble barium sulfate is precipitated. The hot reaction mixtures is filtered over Celite. The filtrate is evaporate in vacuo. The residue is treated with ether and filtered again. The solid is washed on the filter with a 2:1 mixture of acetone and water and dried until constant weight. Thus 0.98 g of primycin palmitate are obtained, yield 82.2%. Mp.: 180-181° C., /α/D25 +30.

Workup

  1. customprecipitate
  2. additionTo the solution thus obtained 2.51 ml of a saturated barium hydroxide solution are added
  3. filtrationThe precipitated barium salt is filtered
  4. temperatureThe reaction mixture is heated
  5. waitto boiling for an hour
  6. customthe insoluble barium sulfate is precipitated
  7. customThe hot reaction mixtures
  8. filtrationis filtered over Celite
  9. customThe filtrate is evaporate in vacuo
  10. additionThe residue is treated with ether
  11. filtrationfiltered again
  12. washThe solid is washed on the
  13. filtrationfilter with a 2:1 mixture of acetone and water
  14. customdried until constant weight

Sources & evidence

ORD record
ord-552cb9d864894fe8b4ce12a6607cac70
Source dataset
uspto-grants-1991_06
Patent number
US05023242

Reaction notes

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